[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]C(Cl)(Cl)Cl)=[CH:4][N:3]=1>CN(C=O)C.O.[Cu]I>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[S:15][C:4]=2[N:3]=1A solution of 2,4-dichloro-5-(2-((trichloromethyl)thio)phenyl)pyrimidine (0.618 g, 1.650 mmol) and copper(I) iodide (0.031 g, 0.165 mmol) in DMF (24.63 ml) was degassed with nitrogen and heated at 110° C. overnight. The reaction solution was cooled to room temperature, diluted with water and filtered. The resulting brown solids were washed with water and a small volume of EtOH. The aqueous layer was extracted twice with EtOAc, combined with the solids, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel, eluted with 10-20% EtOAc/heptanes (v/v), affording 0.14 g (38% yield) of the 2-chlorobenzo[4,5]thieno[2,3-d]pyrimidine as white solids.
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